p-Toluenesulfonic acid monohydrate → tetrahydro-3-hydroxy-(R)-6-undecyl-2H-pyran-2-one

HRID 6057ノート

反応式

HRID 6057 の反応式
C([C@H](C(O)CC([O:25][CH:26]1[CH2:31][CH2:30][CH2:29][CH2:28][O:27]1)CCCCCCCCCCC)C(O)=O)CCCCC.[OH2:33].[C:34]1([CH3:44])[CH:39]=[CH:38][C:37](S(O)(=O)=O)=[CH:36][CH:35]=1>C(O)C>[OH:33][C@@H:31]1[CH2:30][CH2:29][CH:28]([CH2:28][CH2:29][CH2:30][CH2:31][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:34][CH3:44])[O:27][C:26]1=[O:25]

参加物

4

反応物 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 678557542-hexyl-3-hydroxy-(R)-5-[(tetrahydro-2H-pyran-2-yl)oxy]hexadecanoic acid

生成物 1

HCID 67855761tetrahydro-3-hydroxy-(R)-6-undecyl-2H-pyran-2-one

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

M)a) 15.4 g of a diastereomer mixture of 2-hexyl-3-hydroxy-(R)-5-[(tetrahydro-2H-pyran-2-yl)oxy]hexadecanoic acid were dissolved in 160 ml of ethanol and 800 mg of toluene-4-sulfonic acid monohydrate were added. The reaction mixture was heated to 55°-60° C. until the reaction was finished. The solvent was removed in vacuo and the residue was dissolved in 160 ml of dichloromethane. The solution was stirred at room temperature for 1 hour. The reaction mixture was evaporated. The material obtained was chromatographed on silica gel. There was obtained tetrahydro-3-hydroxy-(R)-6-undecyl-2H-pyran-2-one, m.p. 95°-96° C.

後処理

  1. temperatureThe reaction mixture was heated to 55°-60° C. until the reaction
  2. customThe solvent was removed in vacuo
  3. dissolutionthe residue was dissolved in 160 ml of dichloromethane
  4. customThe reaction mixture was evaporated
  5. customThe material obtained
  6. customwas chromatographed on silica gel

出典と根拠

ORDレコード
ord-79667b592cd94ca2943c996933ceac25
出典データセット
uspto-grants-1993_09
特許番号
US05246960

反応ノート

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